Thionyl Chloride → HCID 21404536, compound

HRID 972694Notes

Reaction equation

HRID 972694 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([C:12]3[NH:13][C:14](=[O:21])[C:15](=[CH:19][CH:20]=3)[C:16](O)=O)[CH:9]=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:24])=O>>[ClH:24].[N:1]1([C:6]2[CH:7]=[C:8]([C:12]3[NH:13][C:14](=[O:21])[C:15](=[CH:19][CH:20]=3)[CH2:16][Cl:24])[CH:9]=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21404513HCID 21404513, compound

Product 1

HCID 21404536HCID 21404536, compound

Procedure

The 6-[m-(1-Pyrrolidinyl)phenyl]-1,2-dihydro-2-oxonicotinic acid (1.9 g.) is suspended in 40 ml. thionyl chloride and stirred at room temperature for 4 hours. A trace of undissolved solid is removed by filtration and the filtrate is diluted with 500 ml. of hexane. A gum which forms at first changes to a tan solid on continued stirring. The solid 6-[m-(1-pyrrdidinyl)phenyl]-1,2-dihydro-2-oxonicotinyl chloride hydrochloride is collected quickly by filtration and dried over phosphorus pentoxide overnight in vacuo. The 1.8 g. of product so obtained is taken on the the next step without further purification.

Workup

  1. customA trace of undissolved solid is removed by filtration
  2. additionthe filtrate is diluted with 500 ml
  3. filtrationThe solid 6-[m-(1-pyrrdidinyl)phenyl]-1,2-dihydro-2-oxonicotinyl chloride hydrochloride is collected quickly by filtration
  4. dry with materialdried over phosphorus pentoxide overnight in vacuo
  5. customof product so obtained
  6. customwithout further purification

Sources & evidence

ORD record
ord-c9ac899633a04f618a124708d4de7bc1
Source dataset
uspto-grants-1977_10
Patent number
US04053470

Reaction notes

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